


Pretty

by KaylaAnne2



Category: Supernatural
Genre: Cas in a dress, Cute, Destiel - Freeform, Fluff, Hurt!Cas, Kissing, M/M, cas just likes dresses, hurt/comfort (slightly), pretty!cas
Language: English
Status: Completed
Published: 2019-08-16
Updated: 2019-08-16
Packaged: 2020-09-02 09:56:47
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,029
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20274052
Author URL: https://archiveofourown.org/users/KaylaAnne2/pseuds/KaylaAnne2
Summary: Cas changes his wardrobe now that he has properly gone shopping. Dean is more than a little shocked by Cas's choice of dress.





	Pretty

**Author's Note:**

> Trigger Warnings: None
> 
> If I missed any warnings, make sure to let me know, please and thank you. Otherwise, enjoy the fic!

When Sam had volunteered to go with Cas to buy new clothes while Dean finished up a simple salt and burn, Dean hadn't expected Cas to be wearing the clothes when he returned. The clothes that Dad would have actually killed Dean for if he ever even looked at them for too long. But the smile on Cas's face as he twirled for Dean (as per Sam's request) in his black, flowery dress with a tight-necked collar that fanned out so beautifully as Cas twirled, revealing the black mesh and some pumped up shoes. It all perfectly complimented Cas's black hair and brought out Cas's eyes with the blue flowers.

"Wow," Dean whispers in awe, unaware that the word left his mouth until Cas looks up with hopeful eyes that shine brighter under Dean's steadfast gaze.

After a while, Dean clears his throat and rubs the back of his neck as he looks down, shuffling a bit before leaving the room.

\--

The next day when Dean goes out to make them a huge pot of coffee and sit down to drink his first cup, Cas comes out in another one of his new outfits, causing Dean to abruptly spit out his first sip all over the counter.

Cas is in a flowy white dress that goes down to his ankles with a big brown belt around his waist. His feet are in a pair of light grey fashion boots that matched the color of Cas's sun hat.

Dean actually thinks that Cas looks  _ pretty _ , but he's not sure why Cas decided to have such an extreme shift in dress from his usual blue tie, button-up, and black slacks. Not to mention that Cas has stopped wearing his signature trench coat.

Cas looks at him with as much hope as yesterday as he twirls yet again and Dean maintains eye contact in stunned awe before feeling awkward and reacting in the same way.

"There's coffee in the pot, help yourself," Dean mutters before leaving the room with his own mug.

\--

"Dude, Cas is acting...weird," Dean says on the third day with Cas wearing a flowy blue, knee-high dress with an off-the-shoulder style.

"Weird as in...happy?" Sam asks, seeming confused.

"No, I mean, yes. He's happier and more hopeful, but also this dress thing."

"What about his dresses?"

"It's just...weird, man. He's never shown interest in that stuff before."

"Does it really matter? He's happy. Just let him be."

"But-"

"No, Dean," Sam insists, glaring at Dean now. "I know that you think about Dad when you see men not conforming to social conventions, to the typical patriarchal form of society, but it really shouldn't matter. Cas was so excited to show you his new wardrobe, kept going on about how you might like him better like that and you keep ignoring him. I see the way you look at him, so just tell him. Or at least compliment him, it's the least you could do."

Dean has rarely heard Sam get so passionate about something, but Sam does advocate for equality apart from the reality they were taught as kids, something Dean has always admired.

"Okay," Dean says and that was that.

\--

The next day, Cas walks in with a rumpled dress shirt and his usual blue tie (although very loose around the neck today) and black slacks with dark circles under his eyes which are avoiding Dean's.

"Hey, Cas. Where's one of the new outfits? Run out already?" Dean asks and Cas only shakes his head, grabbing coffee and plopping down. "Didn't feel like it?"

"No, Dean, I really didn't feel like another rejection today," Cas snaps, causing Dean to be confused, thinking over Sam’s words from yesterday.

"Why would you be rejected, buddy? You look really pretty, so how could they reject you?" Dean asks, finally plucking up the courage to tell Cas what he thinks.

" _ You _ did, Dean. You don't like me when I look like this or when I wear dresses and I know that you think men shouldn't wear those clothes, but they felt nice. But you still don't like me, you didn't even  _ talk  _ to me in the dresses, so I gave up," Cas says.

"Did you hear what I said?" Dean asks with a small smile.

"Yes, you called me pretty, but...wait, you think I'm pretty?" Cas asks.

"Yeah. Always. You just looked really happy in the dress and your smile made you look even prettier. I'm just bad at saying it and you stunned me looking all happy and shit that I didn't know what to say."

"You really think I'm pretty?"

Dean moves over to Cas and puts his hands on Cas's waist, sidling up closer to Cas with his cocky smile on his face, done with hiding anymore.

"The prettiest. And if those dresses make you so happy, go back in there and get changed, put that smile back on your face. For now…" Dean leans in and holds eye contact as he connects his lips with Cas's, placing that smile back on his face without a change of clothes. And Dean finds his own bright smile to accompany Cas's.

When they pull back, from each other, Dean wants to lean back in and restrengthen their bond that has now shifted to lovers.

"And makeup?" Cas asks and Dean smiles, leaning back in to gently pull on Cas's bottom lip with own lips in a gentle kiss.

"Yeah, whatever makes you happy, Cas," Dean says and Cas's smile makes it all worth it.

\--

The next day, Cas walks out of his and Dean's room in a beautiful blue floor-length dress and white sandals, all dolled up in makeup that he had actually figured out with the help of hours on the phone with Charlie his first night.

Dean doesn't think that he could be prouder of his boyfriend, proudly wrapping and arm around Cas as he joins Dean at the kitchen table.

When Dean sees Sam's knowing smirk, Dean just kisses Cas on the cheek and smiles. He has finally allowed himself to be happy with Cas. So happy. And that in itself is really pretty.

**Author's Note:**

> Thanks for reading to the end of this fic! If you liked, make sure to leave a kudos and a comment!!


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